The quaternary ammonium and phosphonium salts of halogenated alkene compounds such as 4-chloro-2-butenyl trimethyl ammonium or phosphonium chloride are useful as quaternizing agents in making cationic vinylic monomers useful in the production of polyacrylamides or other polymers that are currently used as flocculants. For example, in the following equation EQU R.sub.3 N + R'Cl.fwdarw.R.sub.3 R'N.sup.+Cl.sup.-
the R'Cl reactant functions as a quaternizing agent in converting the R.sub.3 N into the quaternary salt R.sub.3 R'N.sup.+Cl.sup.-. Thus, cationic vinyl monomers may be produced as, for example, in the following equation ##EQU1##
Such salts are also useful in the production of cationic starches and guar.
Compounds such as 4-halo-2-alkenyl tri-lower alkyl ammonium or phosphonium halide, and particular 4-chloro-2-butenty trimethyl ammonium or phosphonium chloride (both the cis and trans isomers), are of special interest as such quaternizing agents.
Processes for producing 4-chloro-2-butenyl trimethyl ammonium chloride are known in the art.
For example, in the past 4-chloro-2-butenyl trimethyl ammonium chloride has been prepared by reacting in solution 1,4-dichlorobutene-2 and trimethyl amine as illustrated in U.S. Pat. No. 3,689,468. Unfortunately, the use of 1,4-dichlorobutene-2 in this process is objectionable in that the 1,4-dichlorobutene-2 is not commercially available in sufficiently pure form. Thus, relatively expensive purification techniques must be performed on the commercially available 1,4-dichlorobutene-2 or the resulting 4-chloro-2-butenyl trimethyl ammonium chloride is also in relatively impure form and is unsuitable for use in the commercial production of cationic vinyl monomers. Also, commercially available 1,4-dichlorobutene-2 is relatively unstable and does not have a commercially acceptable shelf life (i,e., a shelf life of more than 1 year).